A phosphate tether-mediated, one-pot, sequential ring-closing metathesis/cross-metathesis/chemoselective hydrogenation protocol

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2634-2637

  Venukadasula, Phanindra K M ^a   Chegondi, Rambabu ^a   Suryn, Gregory M ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; HYDROGENATION; STEREOISOMERISM;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; HYDROGENATION; MOLECULAR STRUCTURE; ORGANOPHOSPHATES; STEREOISOMERISM;

EID: 84862099244     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301007h     Document Type: Article

References (41)

1. Wender, P. A.; Verma, V. A. Acc. Chem. Soc. 2008, 41, 40-49
2. Trost, B. M. Science 1991, 254, 1471-1477
3. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281
4. Young, S. I.; Baran, P. S. Nat. Chem. 2009, 1, 193-205
5. Hoffmann, R. W. Synthesis 2006, 3531-3541
6. Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551-564
7. Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
8. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186
9. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581
10. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167-178
11. Ishikawa, H.; Honma, M.; Hayashi, Y. Angew. Chem., Int. Ed. 2011, 50, 2824-2827
12. Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003.
13. Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313
14. Murelli, R. P.; Snapper, M. L. Org. Lett. 2007, 9, 1749-1752
15. Scholte, A. A.; An, M.-H.; Snapper, M. L. Org. Lett. 2006, 8, 4759-4762
16. Seigal, B. A.; Fajardo, C.; Snapper, M. L. J. Am. Chem. Soc. 2005, 127, 16329-16332
17. Fustero, S.; Jimenez, D.; Sanchez-Rosello, M.; del Pozo, C. J. Am. Chem. Soc. 2007, 129, 6700-6701
18. Quinn, K. L.; Curto, J. M.; McGrath, K. P.; Biddick, N. A. Tetrahedron Lett. 2009, 50, 7121-7123
19. Quinn, K. J.; Isaacs, A. K.; Arvary, R. A. Org. Lett. 2004, 6, 4143-4145
20. Virolleaud, M-. A.; Bressy, C.; Piva, O. Tetrahedron Lett. 2003, 44, 8081-8084
21. Virolleaud, M-.A.; Piva, O. Tetrahedron Lett. 2007, 48, 1417-1420
22. Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459-462
23. Ferrie, L.; BouzBouz, S.; Cossy, J. Org. Lett. 2009, 11, 5446-5448
24. Ferrie, L.; BouzBouz, S.; Cossy, J. Org. Lett. 2009, 11, 5446-5448
25. Riache, N.; Blond, A.; Nay, B. Tetrahedron 2008, 64, 10853-10859
26. Cross, F.; Pelotier, B.; Piva, O. Eur. J. Org. Chem. 2010, 5063-5070
27. O'Leary-Steele, C.; Pedersen, P. J.; James, T.; Lanyon-Hogg, T.; Leach, S.; Hayes, J.; Nelson, A. Chem.-Eur. J. 2010, 16, 9563-9571
28. Whitehead, A.; McReynolds, M. D.; Moore, J. D.; Hanson., P. R. Org. Lett. 2005, 7, 3375-3378
29. Thomas, C. D.; McParland, J. M.; Hanson, P. R. Eur. J. Org. Chem. 2009, 5487-5500
30. Venukadasula, P. K. M.; Chegondi, R.; Maitra, S.; Hanson, P. R. Org. Lett. 2010, 12, 1556-1559
31. Hanson, P. R.; Chegondi, R.; Nguyen, J.; Thomas, C. D.; Waetzig, J. D.; Whitehead, A. J. Org. Chem. 2011, 76, 4358-4370
32. Chegondi, R.; Tan, M. M. L.; Hanson, P. R. J. Org. Chem. 2011, 76, 3909-3916
33. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370
34. Waetzig, J. W.; Hanson, P. R. Org. Lett. 2006, 8, 1673-1676
35. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biol. Chem. 2004, 2, 8-23 and references cited therein
36. A study of the CM reaction using the Hoveyda-Grubbs catalyst was reported by: Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 624, 327-332
37. Dewi, P.; Randl, S.; Blechert, S. Tetrahedron Lett. 2005, 46, 577-580
38. 1,4-Benzoquinone is generally used to suppress any Ru-H generated during the metathesis event. CuI is generally used in conjunction with the Grubbs second generation catalyst to scavenge the phosphine and keep open the coordination site at Ru to enhance the rate of the metathesis reaction; Voigtritter, K.; Ghorai, S.; Lipshutz, B. H. J. Org. Chem. 2011, 76, 4697-4702
39. Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507
40. O'Doherty, G. A.; Haukaas, M. H. Org. Lett. 2002, 4, 1771-1774
41. Buszek, K. R.; Brown, N. J. Org. Chem. 2007, 72, 3125-3128